Azo dyestuff and process of making same



Patented July 14, 1925.

KARL THIESS, OF SINDLINGEN, NEAR HOCHST-ON-THE-MAIN, GERMANY, ASSIGNORTO FABBWERKE VORM. MEISTER LUCIUS 80 BR'O'NING, OF HO'OHST-O-N-THE-MAIN,GERMANY, A CORPORATION OF GERMANY.

AZO DYESTUFF AND PROCESS OF MAKING SAME.

No Drawing. Application filed January To all whom it may concern:

Be it known that I, KARL THmss, a citizen of Germany, residing atSindlingen, near Hochst-on-the-Main, Germany, have invented certain newand useful Improvements in Azo Dyestuffs and Processes of Making Same,of which the following is a specification.

I have found that by combining arylamides of the2-hydroxynaphthalene-3-carboxylic acid with the hitherto unknownbenzaldehyde-azo-a-naphthylamineswhich as such are obtained by thecombination of diazotized aminobenzaldehydes with a-naphthylaminescapable of being coupled in 4 position-there can be obtained chieflyblack dye-stuffs of excellent properties as to fastness notwithstandingthe fact that the said dyestuffs contain a free aldehyde group. Thesedyestuifs may be produced as pigment dyes or on a substratum or on thefibre itself. The latter method is carried out in such a manner that thematerial impregnated with arylamides of the2-hydroxynap-hthalene-3-carboxylic acid is treated with a diazo compoundof the benzaldehydeazo-l-naphthylamines.

According to the kind of components used, there are obtainedreddish-black, black to greenish-black dyeings. The fastness of thesedyeings, particularly their fastness to light, may be still enhanced bya treatment with copper salts. As disazo components may be used allaminoazo compounds with a free aldehyde group, which are obtained bycoupling diazotized aminobenzaldehydes, their homologues andsubstitution products with oz-naphthylamine and its derivatives whichare capable of being coupled in 4: position.

The following examples illustrate my invention:

1. Some cotton yarn is impregnated with the following solution: I

12 grams of 2.3-hydroxynaphthoic acid- {fi-naphthylamide, 36 com. ofcaustic soda 34 B., 2 1 ccm. of sodium Turkey-red oil per cent, 500 ccm.of hot water made up with water to 1 litre. The impregnated yarn is 29,1925. Serial No. 5,647.

wound oil and dyed with a diazo solution which has been prepared in thefollowing manner:

5.5 ams of benzaldehydeazo-a-naphthylamme (produced by means of m-aminobenzaldehyde) in the form of a thin-liquid paste, are slowly introduced,while stirring, together with 1.75 grams of sodium nitrite intoice-water and 5 com. of hydrochloric acid 22 B. After the diazotizationis complete, the solution is made up with cold water to one litre andthe whole is neutralized with sodium acetate.

The grounded yarn is left for some time in the dye-bath, then rinsed,soaped and finished. Thus a full black tint with a somewhat red hue isobtained. The dyestufi dissolves in substance in concentrated sulfuricacid to a violet solution.

2. Some cotton yarn is impregnated with the following solution:

12 grams of 2.3-hydroxynaphthoic acid-@- naphthylamide, 86 com. ofcaustic soda solution 34 B., 24 com, of sodium Turkey-red oil 50 percent, 500 ccm. of hot water made upwith water to 1 litre. Theimpregnated yarn is wound 0E and dyed with a diazo solution which hasbeen prepared in the following nianiier:

5.5 grams of benzaldehyde-azo-ocnaphthylamine (produced by means ofp-aminobenzaldehyde) in the form of a thin-liquid paste, are slowlyintroduced, while stirring, together with 1.75 grams of sodium nitriteinto ice-water and 5 ccm. of hydrochloric acid of 22 B. After thediazotization is complete, the solution is made up with cold Water toone litre and the whole is neutralized with sodium acetate.

The grounded yarn is left for some time in the dye-bath, then rinsed,soaped and finished.

Thus a neutral black tint is obtained. The dyestuff dissolves insubstance in concentrated sulfuric acid to a violet solution.

3. The dyeing-process is carried out as Y s ecified in Example 1 withthe exception t at in the resent case 2.3-hydroxynaphthoic acid-a-napthylamide is used, the tint obtained being reddish black. The dyestufidissolves in substance in concentrated sulfuric acid to a greensolution.

As the dyestuffs contain a free aldehyde group, they can be convertedinto compounds soluble in cold Water or hot water by means of bisulfite.

I claim:

1. Process of producing azo dyestuffs, consisting in coupling diazotizedbenzaldehydeazo-oc-naphthylamines with arylamides of the2-hydroxynaphthalene-3-carboxylic acid.

2. Process of producing azo dyestuffs, consisting in coupling diazotizedl-benzaldehyde 3- lazo-1.-amino-naphthalene)' with arylides of the2-hydroxynaphthalene-3-carboxylic acid.

3. Process of producing azo dyestufis, consisting in coupling diazotizedl-benzaldehyde-3- iazo-1-amino-n'aphthalene) with the fi-naphthylamideof the 2-hydroxynaph- A thalene-3-carboxylic acid.

C 4. As new products, azo dyestufls, substant1ally identical with thoseobtainable by coupllng diazotized benzaldehyde-azwabeing a bluish-blackpowder, insoluble in water, soluble in concentrated sulfuric acid with aviolet color, giving with bisulfite soluble compounds.

9. As new articles, textile material dyed naphthylamines with arylamidesof the 2- hydroxynaphthalene-3-carboxylic acid, being reddish tobluish-black powders, insoluble in water, soluble in concentratedsulfuric acid with characteristic shades of color, giving with bisulfitesoluble compounds.

5. As new products, textile material dyed with an azo dyestuff asclaimedin claim 4, the said dyestufl' being formed on the material.v

6. As new products, azo dyestuffs, substantially identical with thoseobtainable by coupling diazotized 1-benzaldehyde-3-(4-azo-1-aminonaphthalene) with arylamides of the2-hydroxynaphthalene-3-carboxylic 4 acid, being reddish to bluish-blackpowders, insoluble in water,'soluble in concentrated sulfuric acid withcharacteristic shades of color.

. 7. As new products, textile material dyed with the azo dyestuffsclaimed in claim 6, the said dyestufi being formed on the material.

8. As a new product, the azo dyestuff of the following formula:

With the azo dyestufi' as claimed in claim 8, the said dyestuff beingformed on the material.

In testimony whereof, I aflix my signature.

KARL THIESS.

